Trailing is a skill plain and simple. I don't think there are any "hard and fast" rules, although there are definately some good guidelines to follow. There are plenty of folks out there with a lot more deer under their belt and years more experience than me, but I've also gotten a schooling in the classroom of hard knocks in 11 short years of bowhunting.
I agree it is important to know where the deer was hit, but I'm also REALLY bad about second guessing myself, and I almost never trust somebody else to know where they hit a deer. Angles play funny tricks on your eyes and low light conditions, target panic (buck fever), among other things make you think you saw things you didn't.
I always like to see the arrow if possible. Everybody knows what a gut shot smells like, and if you've smelled a liver shot you'll remember that one too. I also want to know how the deer ran off and what it did when it ran off.
I am a really slow tracker. I like to go from one drop of blood to the next and I try not to take a forward step until I can see the next drop of blood. Of course this isn't always possible but it greatly slows me down and I find that I pick up tiny specks of blood.
It also comes down to some old Dick Tracey, Ben Mattlock stuff. I found blood on the bottom side of a flipped leaf one time by noticing how the ants were focused on one particular leaf. The blood was almost completly soaked into the dirt and I would have never found it without the ants. That one drop put me back on the trail and 20 mintues later I found the deer.
I trailed a buck last year that never dropped a single speck of blood that I could find. I followed his track through the swamp by breaking off a twig the same length as his track and crawing on my hands and knees until I got to the thicket where he bedded.
It's little things that seem to make the difference for me, and CONFIDENCE. You have to have confidence that you can find 1 more drop of blood. I found another lost trail one time by finding a couple hairs stuck in a barbed wire fence. Five feet past the hair was a drop of blood, another 80 yards was the deer.
Bottom line, I think its a skill honed by experience. You have to be observant, and you can't think you know what is going to happen, leave all the options open.
One last story and then I'm done. A few years ago I climbed down after a good morning on the edge of a swamp. As I was gathering my things at the bottom of the tree I look up and here comes a buck down the trail headed for me. He wasn't a monster but I wanted to see if I could get the drop on him while standing on the ground. I managed to stay hidden behind a tupelo well enough to double lung him at 15 yards. He ran off and I thought I heard him fall. Gave him an hour and started following good blood that turned into the swamp. Then it went dead. Nothing. I'm scratching my head when I notice a buzzard is circling just over the tree tops. I watch him and in a few minutes I had a pretty focused spot he was circling over. I walked over there without seening any blood and the deer was laying on the opposite side of a log. I don't know that I would have ever found him if it weren't for just being observant to what was going on around at the time.
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